This is an unofficial archive of PsychonautWiki as of 2025-08-11T15:14:44Z. Content on this page may be outdated, incomplete, or inaccurate. Please refer to the original page for the most up-to-date information.
DOC: Difference between revisions
>LockPicker m grammar |
>LockPicker m merged redundant references |
||
| Line 3: | Line 3: | ||
'''4-Chloro-2,5-dimethoxyamphetamine''' (also known as '''DOC''') is a lesser-known [[psychoactive class::psychedelic]] substance of the [[chemical class::Substituted amphetamine|amphetamine]] class. It is a member of the [[DOx]] family of psychedelic amphetamines, which are known for their long duration and mixture of psychedelic and stimulant effects. | '''4-Chloro-2,5-dimethoxyamphetamine''' (also known as '''DOC''') is a lesser-known [[psychoactive class::psychedelic]] substance of the [[chemical class::Substituted amphetamine|amphetamine]] class. It is a member of the [[DOx]] family of psychedelic amphetamines, which are known for their long duration and mixture of psychedelic and stimulant effects. | ||
DOC was first synthesized by a team at the University of Alberta in 1972.<ref>Coutts, Ronald T; Malicky, Jerry L. (1973). "The Synthesis of Some Analogs of the Hallucinogen 1-(2,5-Dimethoxy-4-methylphenyl)-2-aminopropane (DOM)". Canadian Journal of Chemistry, 1973, 51(9): 1402-1409, 10.1139/v73-210 | http://www.nrcresearchpress.com/doi/abs/10.1139/v73-210</ref> However, its usage in humans was not popularized until the 1991 publication [[PiHKAL]] ("Phenethylamines I Have Known And Loved") by [[Alexander Shulgin]].<ref name="PiHKAL">http://www.erowid.org/library/books_online/pihkal/pihkal.shtml</ref> Preceding this, a 1989 forensic analysis of designer amphetamine samples identified DOC in Canadian drug seizures.<ref>Brian A. Dawson & George A. Neville (1989) "Identification of Two New 'Designer' Amphetamines by NMR Techniques", Canadian Society of Forensic Science Journal, 22:2, 195-202, https://doi.org/10.1080/00085030.198</ref> | DOC was first synthesized by a team at the University of Alberta in 1972.<ref name="Coutts1973">Coutts, Ronald T; Malicky, Jerry L. (1973). "The Synthesis of Some Analogs of the Hallucinogen 1-(2,5-Dimethoxy-4-methylphenyl)-2-aminopropane (DOM)". Canadian Journal of Chemistry, 1973, 51(9): 1402-1409, 10.1139/v73-210 | http://www.nrcresearchpress.com/doi/abs/10.1139/v73-210</ref> However, its usage in humans was not popularized until the 1991 publication [[PiHKAL]] ("Phenethylamines I Have Known And Loved") by [[Alexander Shulgin]].<ref name="PiHKAL">http://www.erowid.org/library/books_online/pihkal/pihkal.shtml</ref> Preceding this, a 1989 forensic analysis of designer amphetamine samples identified DOC in Canadian drug seizures.<ref name="Dawson1989">Brian A. Dawson & George A. Neville (1989) "Identification of Two New 'Designer' Amphetamines by NMR Techniques", Canadian Society of Forensic Science Journal, 22:2, 195-202, https://doi.org/10.1080/00085030.198</ref> | ||
DOC is known as a highly dose-sensitive psychedelic that is often sold in powder form or on blotting paper and known for its long duration (over 12-24 hours), strong visual effects, a unique form of [[stimulation]], and a significant body load. | DOC is known as a highly dose-sensitive psychedelic that is often sold in powder form or on blotting paper and known for its long duration (over 12-24 hours), strong visual effects, a unique form of [[stimulation]], and a significant body load. | ||
| Line 11: | Line 11: | ||
==History and culture== | ==History and culture== | ||
{{historyStub}} | {{historyStub}} | ||
DOC was first synthesized by 1972 by Ronald Coutts and Jerry Malicky at the University of Alberta<ref | DOC was first synthesized by 1972 by Ronald Coutts and Jerry Malicky at the University of Alberta.<ref name="Coutts1973"/> While human usage was popularized by the 1991 publication of its synthesis and pharmacology in [[PiHKAL]] ("Phenethylamines I Have Known And Loved")<ref name="PiHKAL">http://www.erowid.org/library/books_online/pihkal/pihkal.shtml</ref> by [[Alexander Shulgin]], a 1989 forensic analysis of designer amphetamine samples identified DOC in Canadian drug seizures.<ref name="Dawson1989"/> | ||
==Chemistry== | ==Chemistry== | ||
DOC or 4-chloro-2,5-dimethoxy-amphetamine, is a molecule of the [[substituted amphetamine]] class. Amphetamines are substituted phenethylamines containing a phenyl ring bound to an amino (NH<sub>2</sub>) group through an ethyl chain and a methyl group bound to the alpha carbon R<sub>α</sub>. DOC contains methoxy functional groups OCH<sub>3</sub> attached to carbons R<sub>2</sub> and R<sub>5</sub> and a chlorine atom attached to carbon R<sub>4</sub> of the phenyl ring. DOC is the amphetamine analogue of the phenethylamine [[2C-C]].<ref | DOC or 4-chloro-2,5-dimethoxy-amphetamine, is a molecule of the [[substituted amphetamine]] class. Amphetamines are substituted phenethylamines containing a phenyl ring bound to an amino (NH<sub>2</sub>) group through an ethyl chain and a methyl group bound to the alpha carbon R<sub>α</sub>. DOC contains methoxy functional groups OCH<sub>3</sub> attached to carbons R<sub>2</sub> and R<sub>5</sub> and a chlorine atom attached to carbon R<sub>4</sub> of the phenyl ring. DOC is the amphetamine analogue of the phenethylamine [[2C-C]].<ref name="PiHKAL"/> | ||
==Pharmacology== | ==Pharmacology== | ||